ANNAPOLIS, MARYLAND—Magical. That’s the word that best describes Annapolis and Anne Arundel County at Christmastime. Green garlands, red ribbons and white lights adorn the homes and storefronts of the City’s centuries-old Historic District, creating the cozy feel of a small European town – complete with caroling in the streets, a boat parade along the waters, candlelit walking tours, and a celebration of chocolate in all its forms.

To make it easy for individuals to enjoy the many exciting events and activities that will be taking place in Annapolis and Anne Arundel County throughout the holidays, Visit Annapolis & Anne Arundel County (VAAAC) has put together a list of major events. For a more comprehensive rundown of events large and small, visit

Lights and Leashes Wednesday, November 15 5:00 p.m. to 9:00 p.m. $20 per car Sandy Point State Park, 1100 East College Parkway, Annapolis 410-268-4388

For one night only, dog lovers are invited to bring their pet and walk past the Lights on the Bay displays on foot. The event features more than 70 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. Proceeds benefit the SPCA of Anne Arundel County.

Singer/Songwriter Belinda Fraley Huesman Saturday, November 18 7:00 p.m. to 9:00 p.m. Admission: $100 Chesapeake Arts Center, Studio 194 Theatre, 194 Hammonds Lane, Brooklyn Park, MD 410-636-6597

Inspirational songwriter, singer and storyteller, Belinda Fraley Huesman, accompanied by Colin Rowe, performs in a benefit concert for the Chesapeake Arts Center (CAC). Ms. Huesman has served as the executive director of CAC since 2012. Proceeds will support every aspect of CAC’s art programming and mission – including art education for all ages and abilities, events and year-round exhibitions.

Lights on the Bay Saturday, November 18 through Monday, January 1 5:00 p.m. to 10:00 p.m. nightly, weather permitting $15, car; $50, bus; $30, mini-bus Sandy Point State Park, 1100 East College Parkway, Annapolis 410-268-4388

Don’t miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 70 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. Proceeds benefit the SPCA of Anne Arundel County.

2nd Annual Blue Friday Community Paddle Friday, November 24 9:30 a.m. to 12:30 p.m. Sandy Point State Park, 1100 East College Pkwy, Annapolis 21409 Admission: Visit website 410-919-9402

The Blue Friday Community Paddle is a celebration of Opting for Outside on a day that many individuals traditionally spend inside shopping. It’s a leisure paddle event. All levels of paddlers are welcome. Equipment is available for rental. Presented by Capital SUP.

Charles Dickens’ A Christmas Carol Fridays-Sundays, November 25 to December 31 Fridays, 8:00 p.m.; Saturdays, 2:00 p.m. and 8:00 p.m.; Sundays, 3:00 p.m.; additional performance on Sunday, November 26 at 7:30 p.m. Annapolis Shakespeare Company, 1804 West Street, Suite 200, Annapolis, MD Admission: $30-$48 410-415-3513

Join the ghosts of Christmas Past, Present and Yet to Come as they lead the miserly Ebenezer Scrooge on a journey of transformation and redemption. This world premiere captures the magic and joy of Dickens’ Yuletide classic with Annapolis Shakespeare Company’s signature flair.

Santa Arrives at Greenstreet Gardens Saturday, November 25 11:00 am Greenstreet Gardens, 391 West Bay Front Road, Lothian, MD Admission: Free 410-867-9500

Join us in welcoming Santa to Greenstreet with the help of the Deale Fire Department. Take the opportunity to take your own special photos with Santa in our Winter Wonderland.

Small Business Saturday Saturday, November 25 Downtown Shops and Stores throughout Annapolis, West Annapolis and Anne Arundel County

This is your chance to show local business owners that you care by shopping at their stores. In an age of global markets and capitalism, it’s far too easy for small businesses to struggle and fail, even if they offer superior products and services. We have the power to turn this around. Small Business Saturday encourages people everywhere to change the world little by little by shopping at small businesses on this designated day – and to make a habit of it in the future.

Grand Illumination – Annapolis Tree Lighting Sunday, November 26 5:00 p.m. until 7:00 p.m. Market Space at the Market House, 25 Market Street, Annapolis Admission: Free

Celebrate the start of the holiday season with the annual Annapolis Grand Illumination. Beginning at 5:00 p.m., enjoy talented local ballet dancers as they perform in front of Zachary’s Jewelers while visiting with the Washington Nationals Mascots! The main on-stage program begins at 5:30 p.m. with dancing and carols and ends at 7:00 p.m. with the annual tree lighting. Enjoy hot chocolate, decorate ornaments for the tree, and enjoy local holiday music. The event is operated and sponsored by the Annapolis Jaycees. The organizations will be collecting donations of unwrapped toys and nonperishable goods to benefit local children and families in need.

Holiday Candlelight Stroll Fridays and Saturdays, December 1-2, 8, 15-16 7:30 p.m. Tours depart from the Information Booth at City Dock, Annapolis Admission: Adults, $21; Children ages 3-11, $12; Children 2 and under, free 410-268-7601, ext. 100

Learn about the origin of holiday traditions – including the significance of evergreens, Yule logs, Christmas trees and Santa Claus as you stroll through Annapolis with a festively attired guide. Includes a tour of the Hammond-Harwood House.

Illuminated London Town Fridays and Saturdays, December 1-2, 8-9, 15-16. Rain or shine. 6:00 p.m. to 9:00 p.m. Historic London Town and Gardens, 839 Londontown Road, Edgewater, MD Admission:  $6 for member adults, seniors, and youth; $3 for member children (ages 4 - 6); Free for children 3 and under. $12 for non-member adults; $10 for non-member seniors; $7 for non-member youth (ages 7- 17); $3 for non-member children (ages 4 - 6); Free for children 3 and under. 410-222-1919

Experience the magic of a winter evening at Illuminated London Town! Sip hot cider and roast s'mores beside roaring fires in the Historic Area, included in the price. Explore the gardens, illuminated with festive holiday lights. Discover colonial nighttime and holidays at a candlelit William Brown House, decorated for the season. Enjoy special performances in the gardens each week -- including the Chesapeake Revelers or the Londontowne Symphony Orchestra. The Coffee Table Truck will have hot specialty drinks for sale. Bring the family to celebrate wintertime and the holidays with us at Illuminated London Town! And bring your dogs! Dogwood Acres Pet Retreat is sponsoring a s’mores “pup-cession” stand. Leashed dogs allowed, except in the William Brown House.

Jolly Express Cruise Fridays-Sundays, December 1-3; 8 and 10; 15-17; and 22-24 6:00 p.m., 7:00 p.m. and 8:00 p.m. City Dock, Annapolis Admission: Adults, $23; Children 11 and under, $13 410-268-7600

Enjoy a 45-minute, holiday inspired “sleigh ride” cruise aboard the reindeer antler bedecked Miss Anne. Cruise includes holiday music, hot cocoa and Captain Santa at the helm.

It’s a Wonderful Life Friday-Sunday, December 1-10 and Thursday, December 7 Fridays, 8:00 p.m.; Saturdays, 2:00 p.m. and 8:00 p.m.; Sundays, 2:00 p.m.; and December 7, 8:00 p.m. The Colonial Players, 108 East Street, Annapolis General Admission: $23 410-268-7373

The beloved American Christmas classic comes to life as a live 1940s radio broadcast. With the help of an ensemble that brings a few dozen characters to the stage, the story of idealistic George Bailey unfolds as he considers ending his life one fateful Christmas Eve. Adapted by Joe Landry from the screenplay by Frances Goodrich, Albert Hackett, Frank Capra and Jo Swerling.

U.S. Naval Academy’s Handel’s Messiah Concerts Saturday-Sunday, December 2-3 Saturday, 8:00 p.m.; Sunday, 3:00 p.m. Main Chapel, 108 Blake Road, Annapolis Admission: Varies 410-293-8497

Continuing a long-standing tradition, the USNA Glee Club combines with the Annapolis Symphony Orchestra, and soloists from the Metropolitan Opera Company to present selections from Handel's beloved Messiah on Saturday evening and Sunday afternoon conducted by Dr. Aaron Smith, USNA Director of Musical Activities. This beautifully elegant concert has been broadcast on public television stations both regionally and nationwide.

State House by Candlelight Saturday, December 2 5:00 p.m. to 9:00 p.m. Maryland State House, State Circle, Annapolis Admission: Free

Enjoy this annual open house featuring performances by young musicians and vocalists from throughout Maryland. The oldest State House in continuous legislative use in the nation will be adorned with 24 Christmas trees representing every Maryland county and Baltimore City. Photo identification is required for individuals age 16 and older. This year’s lineup includes:

5:30 – Bates Performing Arts Chorus (Bates Middle School) 6:00 – Institute of Notre Dame Choru 6:30 – Chesapeake Youth Symphony Senior Flute Ensemble 7:00 – All Children's Chorus of Annapolis 7:30 – Allegro Children's Chorus (Easton) 8:00 – Annapolis Area Christian School Madrigal Singers, and Bell Arte 8:30 – Severna Park Middle School Varsity Choir

Captain Santa’s Workshop Saturday, December 2 Session One: 10:00 a.m. to 11:00 a.m.; session two: 11:00 a.m. to noon Annapolis Maritime Museum, 723 2nd Street, Annapolis Admission: $10 for members; $15 for non-members; adults are free 410-295-0104

Create eco-crafts and gifts, including bird feed garlands, up-cycled jingle bells and candles. Enjoy beverages served at the hot cocoa, coffee and popcorn bar. Be sure to have your picture taken with Santa.

A Cantori Christmas Sunday, December 3 3:00 p.m. St. Anne’s Church, 199 Duke of Gloucester Street, Annapolis Admission: Come as you are and pay as you can! 410-263-1906

Conducted by Laurie J. Hays and accompanied by Carolene Winter, Live Arts Maryland’s women’s ensemble performs in a program that includes pieces by Benjamin Britten, Ralph Vaughan Williams, Z. Randall Stroope, John Rutter, Michael Engelhardt and more. Guest musicians include Annapolis Chamber Orchestra member Kerry Willingham on oboe and student percussionists from Annapolis High School.

Tea with the Sugar Plum Fairy and Nutcracker Prince Sunday, December 3 1:00 p.m. Captain Avery Museum, 1418 East West Shady Side Road, Shady Side, MD Admission: Museum members, $20; non-members, $25

Presented by the National Ballet Company and Captain Avery Museum, the Sugar Plum Fairy will read the story of “The Nutcracker” followed by a mini-ballet featuring the Sugar Plum Fairy, Clara, Nutcracker Prince and Mouse King. Following the presentation, the audience will enjoy tea sandwiches and assorted sweet treats. Children will have an opportunity to take a photo with their favorite character. Expect Santa to make an appearance.

3rd Annual Chocolate Binge Festival Sunday, December 3 Noon to 5 p.m. First block of West Street in downtown Annapolis Admission: $5.00 suggested cash donation

Are you a chocoholic in need of a fix? You won’t want to miss the 3rd Annual Chocolate Binge Festival. Two dozen local chocolate vendors will be selling chocolate specialties, including chocolate caramels, cakes, bars, truffles, fudge, cookies, candies, hot chocolate and more. The afternoon also includes family-friendly entertainment, holiday shopping and the lighting of the West Street Holiday Light Canopy. Enjoy live music, roasting S'mores with the Fire Department, a gingerbread house moon bounce, a giant snowball run, Coco with the Popo, and a visit with Santa. He’ll be collecting toys and clothing for the We Care and Friends Holiday Party for kids in need. Presented by the Annapolis Arts District and Inner West Street Association.

Arias & Encores Sunday, December 3 3:00 p.m. Calvary United Methodist Church, 301 Rowe Boulevard, Annapolis Admission: $45; students, $25 410-280-5640

Join Annapolis Opera for its first concert of the 2017 – 2018 season, showcasing a mix of favorite arias and duets from opera and musical theatre, and performed by some of the company’s favorite female singers!

Midnight Madness Holiday Shopping I, II, II Thursdays, December 7, 14 and 21 6:00 p.m. to midnight, 12/7 and 12/14; 6:00 p.m. to 11:00 p.m., 12/21 Downtown Annapolis Admission: Free

Lights, garland, action! Historic Annapolis shops throw open their doors in a glorified block party that’s open to all. Enjoy outside musical performances as well as food and refreshments at many stores as you stroll along Main Street, Maryland Avenue, Inner West Street, and State Circle in search of that perfect gift. To enhance the experience, the first block of Main Street will be closed traffic for the first time this year. Sponsored by the Downtown Annapolis Partnership.

A Celebration of Christmas Friday, December 8 8:00 p.m. Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis Admission: Visit website 410-263-1906

Live Arts Maryland’s J. Ernest Green, the Annapolis Chorale and the Annapolis Chamber Orchestra present a joyous blend of favorite Christmas songs, including “White Christmas” and “It’s the Most Wonderful Time of the Year.' The Annapolis Chamber Orchestra takes center stage for the classic, “Sleigh Ride” and “Twas the Night before Christmas”. The evening includes an audience carol sing-along with Maestro Green.

Spencer Humm’s Baltimore Christmas Special Friday-Sunday, December 8-10 and 15-17 Friday and Saturday, 8:00 p.m.; Sunday, 3:00 p.m. Admission: $35-$55 Chesapeake Arts Center, Studio 194 Theatre, 194 Hammonds Lane, Brooklyn Park, MD 410-636-6597

Baltimore’s most popular Christmas comedy event celebrates its fifteenth season of fun. Join Spencer “Slash” Humm on a journey of outrageous comedy, music and yuletide merriment. The one-of-a-kind production is known for its juggling, magic, stand-up comedy, musical theatre, and more. Come see what tricks they have up their sleeve for this 15th anniversary celebration!

35th Annual Eastport Yacht Club Lights Parade Saturday, December 9 6:00 p.m. to 8:00 p.m. Annapolis Harbor and Spa Creek Admission: Free or 844-463-6392

Dozens of brightly decorated boats parade around the Annapolis waterfront in one of the City’s signature events. Thousands of lights and a host of jolly revelers make this a fun holiday event for the entire family. Prime viewing areas include: Eastport, Spa Creek, City Dock and Naval Academy sea wall. Sponsored by the Eastport Yacht Club.

The Nutcracker Saturday and Sunday, December 9-10, 16-17 Saturday, 7:00 p.m.; Sunday, 1:00 p.m. and 4:30 p.m. Maryland Hall for the Creative Arts, 801 Chase Street, Annapolis Admission: Adult, $52; Senior, $43; Student, $30; child, 10 and under, $30; MHCA Member, $47 410-224-5644

The Ballet Theatre of Maryland invites you to the most famous Christmas Party of all time – “The Nutcracker,” where the possibility of dreams, the magic of Christmas and the wonder of the child merge through young Clara’s adventures with mechanical dolls, life-size rats, and whirling kingdoms of snow and sweets. Help Clara rescue her beloved Nutcracker from the Rat Queen’s evil spell and discover her true destiny.

15th Annual ALS Artisan Boutique Sunday, December 10 10:00 a.m. to 5:00 p.m. Crowne Plaza Annapolis Hotel, 173 Jennifer Road, Annapolis, MD Admission: Free 410-991-4959

More than 55 regional artists will showcase handcrafted jewelry, original children’s clothing and accessories, pottery, paintings and more. The event will also include door prizes, raffles, a silent auction, refreshments and an appearance by Lisa McCue, an illustrator of children’s books, including the Corduroy series. Event benefits patients and families living with ALS.

“The Messiah” Friday through Sunday, December 15-17 St. Anne’s Church, 199 Duke of Gloucester Street, Annapolis Friday and Saturday, 8:00 p.m.; Sunday, 3:00 p.m. Admission: adults, $45 plus $3.50 service fee; students, free through the student rush program 410-263-1906

Live Arts Maryland presents the Annapolis Chorale’s Chamber Chorus and the Annapolis Chamber Orchestra performing Handel’s timeless masterpiece at St. Anne’s Church. Four guest soloists join LAM for this year’s performances: soprano Amy Cofield; mezzo soprano Kathryn Leemhuis; tenor Joseph Regan; and baritone Matthew Anchel.

Fiddler on the Roof Thursday to Sunday, December 15 to Sunday, January 21 Compass Rose Theater, 49 Spa Road, Annapolis Admission: adults, $38; seniors (65 and older) and military, $33; students with ID and children, $23 410-980-6662

Based on the book by Joseph Stein. Music by Jerry Bock, and lyrics by Sheldon Harnick.

Holiday Open House Saturday, December 16 4:00 p.m. to 7:00 p.m. William Paca House and Garden, 186 Prince George Street, Annapolis Hogshead, 43 Pinkney Street, Annapolis Admission: Free for HA members and volunteers; $10 for non-members 410-267-7619

Come join William and Mary Paca for a festive occasion as they welcome you to their home and entertain for the holidays! Living historians will bring the house of the Declaration of Independence signer to life with laughter, games, music and sweet treats to share! At Hogshead, visitors will see how middling sorts – played by living historians – celebrate the holiday season with a variety of fun activities for the whole family. Light refreshments are included. Reservations encouraged.

Winter Wonderland and Decorations Galore Family Workshop Saturday, December 16 10:00 a.m. to 1:00 p.m. Chesapeake Arts Center’s MakerSpace, 194 Hammonds Lane, Brooklyn Park, MD Admission: Pay what you can 410-636-6597

A free winter wonderland event! Laser cut snowflakes, decorate table top trees, paint ornaments and get holiday ready!

Yule Log Centerpieces – Make and Take Sunday, December 17 1:00 p.m. to 4:00 p.m. Captain Avery Museum, 1418 East West Shady Side Road 410-867-4486

Drop by and create a festive Yule Log centerpiece using fresh-cut greenery. Joanne and Chrissy from Art House 20765 will lead a workshop culminating with the creation of your own Yule Log, ready to adorn your holiday table. Reservations required. Workshops will run every half hour with ten individuals per time slot. To guarantee a space, a $6 non-refundable deposit will be applied toward your purchase. Children under the age of ten must be accompanied by an adult.

Military Bowl Thursday, December 28 1:30 p.m. U.S. Navy-Marine Corps Memorial Stadium, 550 Taylor Avenue, Annapolis

The Military Bowl presented by Northrop Grumman Corporation, benefitting the USO of Metropolitan Washington-Baltimore (USO-Metro), will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC) in its 10th Anniversary game. The world-famous Budweiser Clydesdales once again will headline the Military Bowl Parade that kicks off gameday festivities – stepping off from Annapolis City Dock at 9:30 a.m.

City of Annapolis New Year’s Eve Celebration Sunday, December 31 3:00 p.m. to 5:30 p.m. kid-friendly activities; 8:00 p.m. to midnight for all Weems Whelan Fields behind Maryland Hall, 801 Chase Street, Annapolis Susan Campbell Park, City Dock, Annapolis Admission: Free 410-263-7997

Family activities fill the day and music and dancing fills the night at this annual celebration welcoming the New Year. For the second year, kids’ activities will take place on Weems Whelan fields behind Maryland Hall and Bates Middle School. Participants are invited to park at Park Place garage and take City of Annapolis-provided shuttles to and from the new location. Activities will include face painting, an obstacle course, moon bounces and music performed by kids’ rock bands. The first round of festivities wraps up with on-site fireworks at approximately 5:30 p.m. Then, it’s off to area restaurants for dinner with the kids. The second round of festivities includes live music and dancing at Susan Campbell Park at City Dock beginning at 8:00 p.m. and ending with midnight fireworks.


VAAAC is a nonprofit, membership-based destination marketing organization that generates revenues for the local economy by promoting Annapolis and Anne Arundel County to leisure and business travelers across the country and around the world.

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